E-1-azabicyclo[2.2.2]oct-3-yl α-(1-bromo-1-propen-3-yl)-α-hydroxy-α-phenylacetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: E-1-azabicyclo[2.2.2]oct-3-yl α-(1-bromo-1-propen-3-yl)-α-hydroxy-α-phenylacetate
• 英文别名: 1-azabicyclo[2.2.2]octan-3-yl (E)-5-bromo-2-hydroxy-2-phenylpent-4-enoate
• 化学式: C₁₈H₂₂BrNO₃
• 分子量: 380.282
• InChiKey: GTPNCABTAXYEMS-ONNFQVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  E-ethyl α-hydroxy-α-phenyl-α-(1-tributylstannyl-1-propen-3-yl)acetate 在 溴 、 sodium 作用下， 以 氯仿 为溶剂， 反应 8.5h， 生成 E-1-azabicyclo[2.2.2]oct-3-yl α-(1-bromo-1-propen-3-yl)-α-hydroxy-α-phenylacetate
  参考文献：
  名称：

  Z-(-,-)-[76Br]BrQNP: A high affinity PET radiotracer for central and cardiac muscarinic receptors

  摘要：

  Racemic E-1-azabicyclo[2.2.2]oct-3-yl alpha-(1-bromo-1-1-propen-3-yl)-alpha-hydroxy-alpha-phenylacetate (BrQNP) was prepared and evaluated in vivo as a potential candidate for imaging muscarinic acetylcholinergic receptors by Positron Emission Tomography. Initial in vivo blocking studies utilizing Z-(-,-)-[I-125]IQNP as a radiolabelled muscarinic probe demonstrated that a preinjection of cold E-BrQNP effectively blocks the uptake of the radiolabelled probe in the brain and heart, by 71% and 86% respectively.Z-(-,-)-[Br-76]BrQNP was prepared by electrophillic substitution from a tributylstannyl precursor. Peracetic acid and chloramine T were evaluated as oxidizing agents. After purification by SPE and RP-HPLC, radiolabelling yields of 85% and 95% were obtained with peracetic acid and chloramine T, respectively. The final radiochemical yield was 70% for both oxidizing agents.Rat biodistribution studies of Z-(-,-)-[Br-76]BrQNP showed high uptake in organs with high concentrations of muscarinic receptors (heart and brain).

  DOI：

  10.1002/(sici)1099-1344(199610)38:10<883::aid-jlcr902>3.0.co;2-x